AU782080B2 - New process for the synthesis of (3aS)-5,5-dioxo-2,3,3a,4-tetrahydro-1H- pyrrolo(2,1-c)(1,2,4)benzothiadiazine - Google Patents
New process for the synthesis of (3aS)-5,5-dioxo-2,3,3a,4-tetrahydro-1H- pyrrolo(2,1-c)(1,2,4)benzothiadiazine Download PDFInfo
- Publication number
- AU782080B2 AU782080B2 AU34405/02A AU3440502A AU782080B2 AU 782080 B2 AU782080 B2 AU 782080B2 AU 34405/02 A AU34405/02 A AU 34405/02A AU 3440502 A AU3440502 A AU 3440502A AU 782080 B2 AU782080 B2 AU 782080B2
- Authority
- AU
- Australia
- Prior art keywords
- formula
- compound
- benzothiadiazine
- pyrrolo
- toluene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims description 15
- 230000015572 biosynthetic process Effects 0.000 title claims description 6
- 238000003786 synthesis reaction Methods 0.000 title claims description 6
- MNTIJYGEITVWHU-SNVBAGLBSA-N (3as)-2,3,3a,4-tetrahydro-1h-pyrrolo[2,1-c][1,2,4]benzothiadiazine 5,5-dioxide Chemical compound C12=CC=CC=C2S(=O)(=O)N[C@@H]2N1CCC2 MNTIJYGEITVWHU-SNVBAGLBSA-N 0.000 title claims description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 20
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 7
- HWOJZNGWXRYGBY-UHFFFAOYSA-N 2,3-dihydro-1h-pyrrolo[2,1-c][1,2,4]benzothiadiazine 5,5-dioxide Chemical compound C12=CC=CC=C2S(=O)(=O)N=C2N1CCC2 HWOJZNGWXRYGBY-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 4
- PONXTPCRRASWKW-ZIAGYGMSSA-N (1r,2r)-1,2-diphenylethane-1,2-diamine Chemical compound C1([C@@H](N)[C@H](N)C=2C=CC=CC=2)=CC=CC=C1 PONXTPCRRASWKW-ZIAGYGMSSA-N 0.000 claims description 3
- HAVZTGSQJIEKPI-UHFFFAOYSA-N benzothiadiazine Chemical compound C1=CC=C2C=NNSC2=C1 HAVZTGSQJIEKPI-UHFFFAOYSA-N 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- -1 for example Substances 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 238000001953 recrystallisation Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 235000009917 Crataegus X brevipes Nutrition 0.000 claims 1
- 235000013204 Crataegus X haemacarpa Nutrition 0.000 claims 1
- 235000009685 Crataegus X maligna Nutrition 0.000 claims 1
- 235000009444 Crataegus X rubrocarnea Nutrition 0.000 claims 1
- 235000009486 Crataegus bullatus Nutrition 0.000 claims 1
- 235000017181 Crataegus chrysocarpa Nutrition 0.000 claims 1
- 235000009682 Crataegus limnophila Nutrition 0.000 claims 1
- 235000004423 Crataegus monogyna Nutrition 0.000 claims 1
- 240000000171 Crataegus monogyna Species 0.000 claims 1
- 235000002313 Crataegus paludosa Nutrition 0.000 claims 1
- 235000009840 Crataegus x incaedua Nutrition 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 239000002023 wood Substances 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000004770 neurodegeneration Effects 0.000 description 2
- 208000015122 neurodegenerative disease Diseases 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- MGRVRXRGTBOSHW-UHFFFAOYSA-N (aminomethyl)phosphonic acid Chemical compound NCP(O)(O)=O MGRVRXRGTBOSHW-UHFFFAOYSA-N 0.000 description 1
- 102000003678 AMPA Receptors Human genes 0.000 description 1
- 108090000078 AMPA Receptors Proteins 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000019771 cognition Effects 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- PZTVCDSGEXHVBL-ODQAEMFESA-L dichlororuthenium;(1r,2r)-1,2-diphenylethane-1,2-diamine;[1-(2-diphenylphosphanylnaphthalen-1-yl)naphthalen-2-yl]-diphenylphosphane Chemical compound [Cl-].[Cl-].[Ru+2].C1([C@@H](N)[C@H](N)C=2C=CC=CC=2)=CC=CC=C1.C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 PZTVCDSGEXHVBL-ODQAEMFESA-L 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000000494 facilitatory effect Effects 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 230000007257 malfunction Effects 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 230000024587 synaptic transmission, glutamatergic Effects 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0105226A FR2823753B1 (fr) | 2001-04-18 | 2001-04-18 | Nouveau procede de synthese de la (3as)-5,5-dioxo-2,3,3a, 4-tetrahydro-1h-pyrrolo [2,1-c] [1,2,4] benzothiadiazine |
| FR0105226 | 2001-04-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU3440502A AU3440502A (en) | 2002-10-24 |
| AU782080B2 true AU782080B2 (en) | 2005-06-30 |
Family
ID=8862416
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU34405/02A Ceased AU782080B2 (en) | 2001-04-18 | 2002-04-18 | New process for the synthesis of (3aS)-5,5-dioxo-2,3,3a,4-tetrahydro-1H- pyrrolo(2,1-c)(1,2,4)benzothiadiazine |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US6518422B2 (enExample) |
| EP (1) | EP1251132B1 (enExample) |
| JP (1) | JP4011956B2 (enExample) |
| KR (1) | KR100468066B1 (enExample) |
| CN (1) | CN1169811C (enExample) |
| AR (1) | AR036871A1 (enExample) |
| AT (1) | ATE269339T1 (enExample) |
| AU (1) | AU782080B2 (enExample) |
| BR (1) | BR0201307A (enExample) |
| CA (1) | CA2382405C (enExample) |
| DE (1) | DE60200627T2 (enExample) |
| DK (1) | DK1251132T3 (enExample) |
| EA (1) | EA004927B1 (enExample) |
| ES (1) | ES2223031T3 (enExample) |
| FR (1) | FR2823753B1 (enExample) |
| HU (1) | HUP0201256A3 (enExample) |
| MX (1) | MXPA02003639A (enExample) |
| NO (1) | NO20021768L (enExample) |
| NZ (1) | NZ518422A (enExample) |
| PL (1) | PL353512A1 (enExample) |
| PT (1) | PT1251132E (enExample) |
| SI (1) | SI1251132T1 (enExample) |
| ZA (1) | ZA200203085B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2856065B1 (fr) * | 2003-06-13 | 2005-08-19 | Servier Lab | Nouveaux derives de benzothiazine et benzothiadiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| US20060014887A1 (en) * | 2004-07-19 | 2006-01-19 | 3M Innovative Properties Company | Method of hydrolyzing a dispersion of ionic fluoropolymer |
| FR2879201B1 (fr) * | 2004-12-10 | 2007-02-16 | Servier Lab | Nouveaux derives de benzothiazine et benzothiadiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| EP2230094B1 (de) | 2009-03-20 | 2013-12-11 | Kremstal Türenwerk GmbH | Verfahren für das Beschichten von Plattenwerkstoffen |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0692484A1 (fr) * | 1994-07-12 | 1996-01-17 | Adir Et Compagnie | Nouveau dérivé de benzothiadiazine, son procédé de préparation et les compositions pharmaceutiques qui le contiennent |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3294791A (en) * | 1966-03-14 | 1966-12-27 | American Home Prod | Tetrahydro-2, 5-methano-1, 2, 5-benzothiadiazepine 1, 1-dioxide |
| US3471483A (en) * | 1967-11-09 | 1969-10-07 | American Home Prod | 1 - substituted - 2,3,3a - 4 - tetrahydro - 1h-pyrrolo(2,1 - c)(1,2,4)benzothiadiazine,5,5-dioxide |
| JPH06192272A (ja) * | 1992-12-24 | 1994-07-12 | Japan Tobacco Inc | 新規なトリアゾロベンゾチアジアジン及びトリアゾロベンゾチアジアゼピン誘導体 |
| FR2812291B1 (fr) * | 2000-07-28 | 2002-12-13 | Adir | Nouveaux derives de benzothiadiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
-
2001
- 2001-04-18 FR FR0105226A patent/FR2823753B1/fr not_active Expired - Fee Related
-
2002
- 2002-04-10 MX MXPA02003639A patent/MXPA02003639A/es active IP Right Grant
- 2002-04-15 NO NO20021768A patent/NO20021768L/no not_active Application Discontinuation
- 2002-04-16 DK DK02290946T patent/DK1251132T3/da active
- 2002-04-16 PT PT02290946T patent/PT1251132E/pt unknown
- 2002-04-16 ES ES02290946T patent/ES2223031T3/es not_active Expired - Lifetime
- 2002-04-16 AT AT02290946T patent/ATE269339T1/de not_active IP Right Cessation
- 2002-04-16 SI SI200230015T patent/SI1251132T1/xx unknown
- 2002-04-16 DE DE60200627T patent/DE60200627T2/de not_active Expired - Fee Related
- 2002-04-16 EP EP02290946A patent/EP1251132B1/fr not_active Expired - Lifetime
- 2002-04-16 JP JP2002113278A patent/JP4011956B2/ja not_active Expired - Fee Related
- 2002-04-17 EA EA200200378A patent/EA004927B1/ru not_active IP Right Cessation
- 2002-04-17 NZ NZ518422A patent/NZ518422A/xx unknown
- 2002-04-17 BR BR0201307-0A patent/BR0201307A/pt not_active IP Right Cessation
- 2002-04-17 HU HU0201256A patent/HUP0201256A3/hu unknown
- 2002-04-17 AR ARP020101386A patent/AR036871A1/es not_active Application Discontinuation
- 2002-04-18 KR KR10-2002-0021237A patent/KR100468066B1/ko not_active Expired - Fee Related
- 2002-04-18 PL PL02353512A patent/PL353512A1/xx unknown
- 2002-04-18 US US10/125,192 patent/US6518422B2/en not_active Expired - Fee Related
- 2002-04-18 CA CA002382405A patent/CA2382405C/fr not_active Expired - Fee Related
- 2002-04-18 AU AU34405/02A patent/AU782080B2/en not_active Ceased
- 2002-04-18 CN CNB021057907A patent/CN1169811C/zh not_active Expired - Fee Related
- 2002-04-18 ZA ZA200203085A patent/ZA200203085B/xx unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0692484A1 (fr) * | 1994-07-12 | 1996-01-17 | Adir Et Compagnie | Nouveau dérivé de benzothiadiazine, son procédé de préparation et les compositions pharmaceutiques qui le contiennent |
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